I like to joke around with customers.
Look at my handle. Duh.
But anyways, I DO joke around with them, and most of them love it and many have come back to my establishment because of me and my wit and sense of humor. This is not bragging, this is simply fact.
But yes, even I on occasion have misread a tight-assed humorless stick in the mud as actually having a sense of humor, and have had one or two complaints about me. Generally speaking, management's answer has usually been something along the lines of "Jester is a good server, and he was only trying to joke around with you. We apologize if you took it the wrong way, but we assure you, he meant nothing disrespectful by it."
And even with those few complaints, I am not going to stop making jokes. It is what I do. It is one reason I don't think I want to work in fine dining, or at any place that takes itself too damn seriously.
I do NOT agree with the people here who say you should never make jokes at work, or that you should keep it to the bare minimum of conversation. If you are someone who jokes around, continue being yourself, by all means.
One caveat: I DO work in the food service industry, and that is somewhat different than retail, so keep that in mind. That being said, I will often make a joke/smartass crack right at the beginning of the customer's time in my station, before I may have had a time to properly read them. Invariably, those are the ones that have gotten me into trouble.
I also think that the SC in the OP was getting bent out of shape over a pretty much harmless joke about a fairly common stereotype, whatever you may think of the stereotype. Two guys joking about women spending all their money is nothing new, and does not denote either guy as chauvinistic or derogatory, in my opinion. It is no different than two women talking about guys being slobs, even though not all guys ARE slobs.
And yes.. women do tend to spend more money shopping than men, especially on clothing/accessories. When you see something cute.. it's just SO hard to resist! Men will never understand.
Um, put me in a bicycle store, magic shop, music store, or book store, and TRUST me, I DO understand!